I have to carry my boots on the plane. Will they let me carry the boots in a boot bag and also carry on a backpack?
Tellruride, How to pack for the plane?
Also, if you're flying into Montrose or Telluride, only small regional jets fly in there, so they often make you door-check your carry-on if it's large because there is very little space in those planes. So it would be tough to even "smuggle" two large carry-on's if you tried.
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I usually carry my transpac which is a not small backpack and a regular sized rolling carry-on. If you have to check at the door of a small plane it is just getting put right on that plane in the cargo bay so you don't have to worry that it will end up flying to Vail when you are flying to Big Sky.